Printed chord notation in almost every musical genre is generally vague and incomplete. It's impossible to be specific for two reasons. One, complexity, in that chord symbols are merely shorthand for a much deeper description of chord content that can change too rapidly to keep up with, and two, the subtleties of context.

Take a straight C Major chord as an example. If you were playing Texas Swing style jazz, it's inferred that you have the license and liberty of adding a Maj 6 or 6/9 extension, and you'd be right in style. If you were playing more progressive Modal Jazz, this sound would be quite corny and out of place; you're more likely to add an Augmented 11th and improvise around a Lydian Scale (Major Scale with raised 4th scale degree.)

You really can't know these nuances without extensive listening. It's a complex thing not easily expressed on paper. Jazz is such an oral tradition, anyway. If you're going to be speaking the language, it's crucial to know the terrain and something about its indigenous natives.

We suggest listening to 3 hours of music to every 1 hour of practicing.

There's also the issue of conflicting extensions. A +9 or b9 might be completely appropriate in a song, but not if another player has made a choice different than yours. Again, it's the art of listening, and the beautiful way musicians intuitively interact, anticipate, and communicate at split-second speed.